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Hydrochloric Acid → 3-Chloro-6-cyclopentyl-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

HRID 1453328
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HRID 1453328 반응식
[CH2:1]([C:5]1([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[O:10][C:9](=[O:11])[CH:8]([Cl:12])[C:7](=[O:13])[CH2:6]1)[CH2:2][C:3]#[CH:4].I[C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.Cl>CN(C=O)C.C(NC(C)C)(C)C.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:12][CH:8]1[C:7](=[O:13])[CH2:6][C:5]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)([CH2:1][CH2:2][C:3]#[C:4][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[O:10][C:9]1=[O:11]
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참가 물질

9

반응물 3

HCID 313Hydrochloric AcidHCID 122723-IodophenolHCID 224997916-But-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione

생성물 1

HCID 587622273-Chloro-6-cyclopentyl-6-[4-(3-hydroxy-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매
HCID 7912Diisopropylamine용매

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온도
90 °C

실험 절차

A solution of 6-but-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione (200 mg, 0.66 mmol) from Step 4 above, 3-iodophenol (145 mg, 0.66 mmol), bis(triphenylphosphine)palladium (II) dichloride (18 mg, 0.026 mmol), and copper (I) iodide (10 mg, 0.052 mmol) in DMF (0.66 mL) and diisopropylamine (0.66 mL) was sonicated for 1 minute and then heated to 90° C. for 20 minutes. The reaction was cooled to room temperature, and then diluted with 10 mL CH2Cl2 The reaction was then neutralized to a pH of 4 with 6 N HCl and the layers were separated. The aqueous layer was extracted with 3×10 mL CH2Cl2 and the organic layers were combined, and then dried over sodium sulfate. After filtering the solids, the organic layer was concentrated to a dark oil, which was used without further purification. MS (ESI): 359 (M−H), 361 (M+2−H).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with 3×10 mL CH2Cl2
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtering the solids
  6. concentrationthe organic layer was concentrated to a dark oil, which
  7. customwas used without further purification

출처 및 근거

ORD 기록
ord-6f83910178fe4c869d813fa15c162d47
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07473790B2

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